Question 1

Which is the more stable form of acetophenone?

Accepted Answer

A) Only I 
B) Only II 
C) Only III 
D) I and II are equally stable 
A) Only I 
B) Only II 
C) Only III 
D) I and II are equally stable B

Question 2

The reaction below is a direct enolate alkylation.It has been found that this reaction only works well with unhindered methyl and 1° alkyl halides.Pick the statement that best explains this observation.

Accepted Answer

A) The nucleophilic enolate requires a reaction center that has a positive charge. 
B) Hindered alkyl halides do not undergo SN1 reactions. 
C) Hindered alkyl halides do not undergo SN2 reactions. 
D) Methyl and 1° alkyl halides can form carbocations that can readily react with the nucleophilic enolate. 
A) The nucleophilic enolate requires a reaction center that has a positive charge. 
B) Hindered alkyl halides do not undergo SN1 reactions. 
C) Hindered alkyl halides do not undergo SN2 reactions. 
D) Methyl and 1° alkyl halides can form carbocations that can readily react with the nucleophilic enolate. C

Question 3

What is (are)the product(s)of the following reaction?

Accepted Answer

A) Only I 
B) Only II 
C) Only III 
D) Only I and III 
A) Only I 
B) Only II 
C) Only III 
D) Only I and III D

Question 4

What is the product of the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 5

Vitamin C is a stable enediol.Which is the structure of a possible keto form in equilibrium with the enediol form?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 6

Which is the thermodynamic enolate of 2-methylcyclohexanone?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 7

Which is the most stable form of 1,3-cyclohexanedione?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 8

Which of the following ketones will give a positive iodoform test?

Accepted Answer

A) 3-Heptanone 
B) 2-Pentanone 
C) 3-Hexanone 
D) Cyclohexanone 
A) 3-Heptanone 
B) 2-Pentanone 
C) 3-Hexanone 
D) Cyclohexanone

Question 9

Which of the following is the most acidic compound?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 10

Which of the following is the intermediate for halogenation of ketones under acidic conditions?

Accepted Answer

A) An enolate 
B) An enol 
C) A tautomer 
D) An epimer 
A) An enolate 
B) An enol 
C) A tautomer 
D) An epimer

Question 11

Which of the following is a possible enol form of 2-butanone?

Accepted Answer

A) I 
B) II 
C) III 
D) II and III 
A) I 
B) II 
C) III 
D) II and III

Question 12

Will acetone be completely deprotonated by potassium tert-butoxide?

Accepted Answer

A) Yes 
B) No 
A) Yes 
B) No

Question 13

What is the starting material in the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 14

Why is it difficult to stop the halogenation of ketones under basic conditions at the mono-halogenated stage?

Accepted Answer

A) The ketone undergoes a Bayer-Villigar oxidation. 
B) The ketone is reduced. 
C) The ketone undergoes an Aldol reaction. 
D) The bromine helps to stabilize the second enolate,making the product more acidic than the starting material. 
A) The ketone undergoes a Bayer-Villigar oxidation. 
B) The ketone is reduced. 
C) The ketone undergoes an Aldol reaction. 
D) The bromine helps to stabilize the second enolate,making the product more acidic than the starting material.

Question 15

What is the structure of X,product of the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 16

What is the starting material required to accomplish the following transformation?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 17

Select the appropriate sequence of reactions to accomplish the following synthesis.

Accepted Answer

A) [1] Br2,CH3CO2H; [2] Li2CO3,LiBr,DMF; [3] CH3CH2CH2CH2Br 
B) [1] Br2,CH3CO2H; [2] Mg,Et2O; [3] CH3CH2CH2CH2Br 
C) [1] LDA; [2] BrCH2CH2CH2CH2Br; [3] NaOEt 
D) [1] NaOEt; [2] BrCH2CH2CH2CH2Br; [3] LDA 
A) [1] Br2,CH3CO2H; [2] Li2CO3,LiBr,DMF; [3] CH3CH2CH2CH2Br 
B) [1] Br2,CH3CO2H; [2] Mg,Et2O; [3] CH3CH2CH2CH2Br 
C) [1] LDA; [2] BrCH2CH2CH2CH2Br; [3] NaOEt 
D) [1] NaOEt; [2] BrCH2CH2CH2CH2Br; [3] LDA

Question 18

What is the product of the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 19

If you want to form a thermodynamic enolate,you want to

Accepted Answer

A) keep the reaction as cold as possible. 
B) use an aprotic solvent such as THF. 
C) use a protic solvent such as ethanol. 
D) use a carboxylic acid. 
A) keep the reaction as cold as possible. 
B) use an aprotic solvent such as THF. 
C) use a protic solvent such as ethanol. 
D) use a carboxylic acid.

Question 20

A simple chemical test to distinguish between acetone and 3-pentanone would be the reaction of the compounds with

Accepted Answer

A) bromine with acetic acid. 
B) bromine and aqueous hydroxide ion. 
C) THF,LDA at -78 °C followed by reaction with bromine. 
D) base and methyl bromide. 
A) bromine with acetic acid. 
B) bromine and aqueous hydroxide ion. 
C) THF,LDA at -78 °C followed by reaction with bromine. 
D) base and methyl bromide.

Exam 21: Substitution Reactions of Carbonyl Compounds at the a Carbon

Which is the more stable form of acetophenone?

The reaction below is a direct enolate alkylation.It has been found that this reaction only works well with unhindered methyl and 1° alkyl halides.Pick the statement that best explains this observation.

What is (are)the product(s)of the following reaction?

What is the product of the following reaction?

Vitamin C is a stable enediol.Which is the structure of a possible keto form in equilibrium with the enediol form?

Which is the thermodynamic enolate of 2-methylcyclohexanone?

Which is the most stable form of 1,3-cyclohexanedione?

Which of the following ketones will give a positive iodoform test?

Which of the following is the most acidic compound?

Which of the following is the intermediate for halogenation of ketones under acidic conditions?

Which of the following is a possible enol form of 2-butanone?

Will acetone be completely deprotonated by potassium tert-butoxide?

What is the starting material in the following reaction?

Why is it difficult to stop the halogenation of ketones under basic conditions at the mono-halogenated stage?

What is the structure of X,product of the following reaction?

What is the starting material required to accomplish the following transformation?

Select the appropriate sequence of reactions to accomplish the following synthesis.

What is the product of the following reaction?

If you want to form a thermodynamic enolate,you want to

A simple chemical test to distinguish between acetone and 3-pentanone would be the reaction of the compounds with

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols,ethers,and Related Compounds

Alkenes and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation, resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives - Nucleophilic Acyl Substitution

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

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